6 Best SaaS Event-Based Gamified & Milestone Retention Email Strategies (2025)

💬 This checklist I've created is great for startups from early-stage founders, and for those who work for fast-growing "PLG companies", looking for different ideas for tests/experiments for milestone and event-based emails across various flows (and behavioural triggers across different segments).

Optimisations and test ideas (with examples) for milestone and event-based SaaS emails

💬 I've shared numerous tests below with reference examples - hopefully these optimisations and tactical areas help. :)

This is a good strategic email initiative to consider to help with retention and staying top of mind to users, whilst highlighting the value of key features of the product. 

It can also help with the likes of feature adoption, where you can highlight areas where users may not be utilising the product ‘as well’ to help achieve outcomes. 

Some of my favourites, which I’ve included here, are from Grammarly, Loom and Duolingo. 

Each of them have core components of usage metrics they highlight to users, but they also provide helpful information, content and helpful resources across product features, events, etc. 

Hence, you can turn these emails into helping reduce churn/increase retention, and even help with upsell and product upgrade opportunities.

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• Grammarly is one of the gold standards when it comes to SaaS data usage digest emails like this - always love receiving mine each week to show how I've used it
• Great use of data t highlight best usage, as well as areas to improve my writing (mistakes section)
• What makes this a great reference too is the use of helpful guides/resources - just another smart way to provide value to subscribers

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• Duolingo is another brand that does a great job with this "weekly summary" digest strategy - whilst not necessarily B2B SaaS, they're good to learn from in terms of marketing

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Related to above examples and points around features, you want to share personalised and contextually relevant resources around specific features to users. 

You can send the likes of tips, video tutorials from your YouTube channel/resource library, gifs, workflow optimisations… anything that you deem will provide value. 

Additionally, it’s good to highlight reminders around customer support - sometimes audiences need to be reminded that there is support available to help with any blockers.

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In conjunction with usage and milestone type emails, it’s good to do some sort of year summary email digest. 

And there are two main ways you can go about it: 

1. Like checklist points 1 and 2, send a year summary of specific users and their product/feature usage
2. Even if not hyper-personalised product usage data on specific users or segments, sending some sort of yearly overview of the business is good. 

But why do a tactical initiative like this?

It all comes back down to reminding users of the value of your product offering - and tailoring the context of usage and their goals they’re wanting to achieve.

In the end, this helps with retention, potential upgrades (ARPU), feedback opportunities, etc.

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A great retention and customer appreciation tactic to help users feel valued is automating time-based anniversary emails. 

And they’re very easy to setup - just trigger them 365 days later after the key ‘signup’ period (whether that’s freemium or when they upgraded to a paid plan). 

Key thought: this can also be a good opportunity based on the plan (free or paid) to provide some sort of offer to encourage a user to upgrade. It’s good timing as most users will feel appreciated/a sense of achievement, which helps build a positive emotional rapport with the brand/product.

• Another great example from Grammarly - good way to congratulate users after one year
• Good experiment to include an offer (like they gave below) for their premium plan (especially segments on their free tier)

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This is a pretty big checklist point and deserves a dedicated resource to explain. 

As part of ‘milestone’ periods, you can combine both activity/usage-based reminders alongside core features. 

For example, you want to ideally setup foundational ‘milestone emails’ (i.e. after 7 days, 14 days, 8 weeks, etc), based tailor events based on behaviours - such as feature usage, how active they are, etc.

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• Good reference here from Asana celebrating users with milestones they've completed (tasks finished) - good encouragement to keep using
• They've also included other features to guide users to try

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This is only really a strategic checklist point if you have some sort of gamified strategy in place. 

Even if you don’t have a comprehensive gamification system or strategy, you can keep things simple with creating badges and ‘awards’ based on usage, or the likes of anniversary milestones. 

Many benefits tied to implementing gamified elements, including the likes of gratification, user motivation - which all ties into adoption, retention/loyalty, amongst other positives. 

• Lyft's example here is up there with one of the top ones I've seen
• Also smart they included a referral invite link as part of these emails - a good tactic to test as part of emails like this (or any automation/event flows)